Upcoming Festivals Events

Spooky Sazón: A Halloween Food Truck Fest

 5403 W Irlo Bronson Memorial Hwy 31 Oct 2025
FOOD-DRINKS FREE

Spirit Fest™ Metaphysical & Crystal Expo - Orlando/Osceola

 Osceola Heritage Park 8 Nov 2025
BUSINESS USD 16 TO 23

Pioneer Day

 2491 Babb Rd, Kissimmee, FL 34746-5803, United States 8 Nov 2025
KIDS

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Upcoming Halloween Events

Promenade 6th Annual "Trunk or Treat" Trick or Treating & Car Show

 Promenade at Sunset Walk 25 Oct 2025
CAR-SHOWS FREE

Boo On Broadway

 421 Broadway, Kissimmee, FL, United States, Florida 34741 24 Oct 2025
KIDS

3rd Annual Trunk or Treat by the Kissimmee Woman's Club

 1616 W Oak St, Kissimmee, FL 34741-4080, United States 25 Oct 2025
TRUNK-OR-TREAT

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Upcoming Comedy Events

Live Comedy Show - Orlando Edition

 FAMA STEAKHOUSE 25 Oct 2025
COMEDY USD 13 TO 55

El George Harris Show Tickets Kissimmee FL Silver Spurs Arena (Orlando area)

 Silver Spurs Arena 9 Nov 2025
ENTERTAINMENT

Jeff Dunham

 Silver Spurs Arena 21 Nov 2025
TRIPS-ADVENTURES

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Upcoming Food & Drinks Events

Kissimmee Senior Expo

 Kissimmee Civic Centre 28 Oct 2025
BUSINESS FREE

🚚 Friday Nights at Food Trucks Heaven

 5403 W Irlo Bronson Memorial Highway, Kissimmee, FL, United States, Florida 34746 24 Oct 2025
FOOD-DRINKS

The Wine & Cheese Experience

 Formosa Winery | Island Grove Wine Company 8 Nov 2025
FOOD-DRINKS USD 23 TO 500

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Upcoming Live Music Events

Promenade 3rd Annual Halloween Costume Contest $1000's in Cash & Prizes!

 Promenade at Sunset Walk 31 Oct 2025
CONTESTS FREE

Family and Friends

 FUMA Hookah Lounge 8 Nov 2025
MUSIC USD 13 TO 269

Humanitarian Concert for Myanmar

 Tohopekaliga High School Auditorium 15 Nov 2025
ENTERTAINMENT USD 109 TO 535

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Upcoming New Year Events

"Rocking New Year 2026" FREE Concert, Street Party & Fireworks Spectacular!

 Promenade at Sunset Walk 31 Dec 2025
NEW-YEAR USD 0 TO 72

Family Vision 2026 - Spreading Kindness Together

 Chambers Park Community Center 3 Jan 2026
NEW-YEAR

Krush Brau New Years Eve Party - Free Admission - Reserve Now!

 Krush Brau Park Portal Immersion Center 31 Dec 2025
NEW-YEAR USD 0 TO 117

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Upcoming Christmas Markets & Fairs Events

European Christmas Market - Christkindlesmarkt - Kissimmee

 Krush Brau Park Portal Immersion Center 7 Dec 2025
FREE

Ice Cream for Breakfast with Santa

 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 6 Dec 2025
BREAKFAST-WITH-SANTA

Ice Cream for Breakfast with Santa

 210 S Bass Rd, Kissimmee, FL, United States, Florida 34746 7 Dec 2025
BREAKFAST-WITH-SANTA

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Upcoming Thanksgiving Events

Shine Bright: Fall Family Fest

 Iglesia del Nazareno Casa de Vida 8 Nov 2025
FESTIVALS

Jeff Dunham at Silver Spurs Arena at Osceola Heritage Park

 Silver Spurs Arena at Osceola Heritage Park 22 Nov 2025
TRIPS-ADVENTURES

Tribute To Van Halen - Thanksgiving Eve - November 26th! On Sale Now

 3274 Margaritaville Blvd 26 Nov 2025
THANKSGIVING USD 32 TO 55

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Trending Events in Kissimmee

Hallows Fall Fest 2025

 Krush Brau Park Portal Immersion Center 26 Oct 2025
KIDS USD 0 TO 8

Puzzles Entertainment's Halloween Trivia @ Crush Yard Orlando

 Crush Yard Orlando 29 Oct 2025
HALLOWEEN

Trunk or Treat Fall Carnival!

3181 Pleasant Hill Rd, Kissimmee, FL, United States, Florida 34746 26 Oct 2025
TRUNK-OR-TREAT

Trunk or Treat

5125 Robert McLane Blvd., Kissimmee, FL 24 Oct 2025
TRUNK-OR-TREAT

Osceola Magic - Puerto Rican Heritage Night + Hat Giveaway!

 1875 Silver Spur Lane, Kissimmee, FL, United States, Florida 34744 8 Nov 2025
SPORTS

Creative Together Market Toy Story Christmas

 7470 W Irlo Bronson Memorial Hwy 1 Nov 2025
CHRISTMAS FREE

Sip & Selfcare - Brunch Edition

 Kissimmee Woman's Club 1 Nov 2025
BRUNCH FREE

Sagittarius Season ''An Elegant & Sexy Affair"

 The Amador Gallery Event Venue 20 Dec 2025
USD 0 TO 20

Monster Bulls

 Silver Spurs Arena 13 Feb 2026
TRIPS-ADVENTURES

Halloween Karaoake @ Construction Zone Restaurant

 The Construction Zone Restaurant 31 Oct 2025
KARAOKE FREE

2025 Christmas Winter Festival- FTC Kissimmee

 Florida Technical College - Kissimmee Campus 13 Dec 2025
FESTIVALS FREE

Osceola County Pioneer Days

 2491 Babb Rd, Kissimmee, FL 34746-5803, United States 8 Nov 2025
MUSIC

ORLANDO FASHION KIDS

 4955 Kyngs Heath Rd 1 Nov 2025
KIDS USD 29 TO 50

A Neil Diamond Tribute in Kissimmee FL

 Elks Lodge 7 Feb 2026
ART

Halloween Party

 205 Lakeview dr, Kissimmee, FL, United States, Florida 34741 31 Oct 2025
HALLOWEEN

More things to do in Kissimmee

Festivals
Halloween
Comedy
Food & Drinks
Live Music
Trunk Or Treat
Trick Or Treat
New Year
Christmas Markets & Fairs
Thanksgiving
Christmas Light Displays
Fireworks
Carnivals
Music Festivals
Parades
Pop-Ups